I swear I replied to this...
Montego 19 was the swing keel model, the Montego 20 was the fixed shoal draft otherwise basically same boat. MONTEGO 20 sailboat specifications and details on sailboatdata.com
I recall the 19 that we had (father bought new in 1979 I think), was a sturdy little boat for it's size. 3 stayed rig with swept spreaders. Backstay was an afterthought.
Boat wasn't a rocket ship in light air, needed 15 knots to really get in the groove. I was very young at the time, probably 8-9 and was just getting into sailing and crewing... but Dad sailed the boat a lot, and thought it was a decent upgrade from his Oday 17 DS.
Sorry can't tell you about point, as I didn't sail it... just crewed, and was 2 young to have an opinion yet. But we sailed it in all kinds of weather from hot 90+ dead summer no wind, to 30 degrees and a small craft warning up. It was tuck a reef and sail on as the weather picked up. I swear it'd sail on its ear all day and stay dry (its actually the boat that broke my fear of heeling at a young age).
But I can say, which is probably quite obvious, the 20, with it's shoal keel, isn't going to point like a J/24. But to learn on it would be good. It's a pretty spacious 19 footer. Faster and lighter than a Compac 19, but easier to tow as well, but again built lighter so the "quality" not as good. Although again my data was of a NEW boat, during the first 3 years of its life, time might have not treated that now 35+ yo boat well.
Can the ranger do it? Probably. I'd want 4x4 though for getting it out of the water (my personal requirement for slippery ramps). 1700lbs boat alone puts the package to about 2300lbs with trailer and gear (just a guess). Shoal keel means deeper in the water than swing, slightly... enough that the rear wheels will likely be wet, hence 4x4. WE slipped ours, but Dad pulled the boat at the end of the season with his Pontiac Bonneville (at the time same as the Caprice)... so if that helps. Again we were in NC at the time, on Lake Norman, so no need to really haul the boat out except for maintenance (and it was new).
I wouldn't want to rig it every time I launched it, but for long weekends or such yeah it'd be OK.
Thing that sticks in my head most about the boat? It had winches that weren't. They were nothing more than winch shaped Clam cleats.